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Carbene-Catalyzed Enantioselective Synthesis of γ-Keto-β-silyl Esters and Amides

Yuxia Zhang, Xuan Huang, Jingcheng Guo, Chenlong Wei, Minghua Gong, Zhenqian Fu

2020Organic Letters27 citationsDOI

Abstract

A variety of γ-keto-β-silyl esters and amides, most with extremely high enantioselectivities, were efficiently prepared via a carbene-catalyzed formal [4 + 2] annulation followed by ring opening with nucleophiles. The resulting compounds from this one-pot strategy can be easily converted into enantioenriched β,σ-dihydroxyl esters.

Topics & Concepts

ChemistryEnantioselective synthesisCarbeneSilylationNucleophileAnnulationCatalysisRing (chemistry)Organic chemistryCombinatorial chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsCyclopropane Reaction Mechanisms
Carbene-Catalyzed Enantioselective Synthesis of γ-Keto-β-silyl Esters and Amides | Litcius